Butyl 2,3,4,6-Tetra-O-benzyl-C-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Butyl 2,3,4,6-Tetra-O-benzyl-C-α-D-glucopyranoside
• 英文别名: α-1,5-anhydro-1-C-butyl-2,3,4,6-tetra-O-benzyl-D-glucitol；(2R,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-butyltetrahydro-2H-pyran；(2R,3S,4R,5R,6R)-2-butyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• 化学式: C₃₈H₄₄O₅
• 分子量: 580.764
• InChiKey: ODSSXMFWBIMGDZ-JTDOPDNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  43
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)dec-6-en-2-ol 在 mercury(II) trifluoroacetate 、 potassium carbonate 、 sodium tetrahydroborate 、 三乙基硼 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以53%的产率得到Butyl 2,3,4,6-Tetra-O-benzyl-C-α-D-glucopyranoside
  参考文献：
  名称：

  A Mitsunobu route to C-glycosides

  摘要：

  C-Glycosides were successfully prepared via dehydrative alkylation under Mitsunobu conditions, using substituted sulfonyl methanes as nucleophiles. The materials prepared were converted to useful C-glycoside intermediates. An application of this approach toward the synthesis of C-glycolipids is presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.024

文献信息

• Tolstikov, G. A.; Prokhorova, N. A.; Spivak, A. Yu., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 10, p. 1858 - 1863
  作者：Tolstikov, G. A.、Prokhorova, N. A.、Spivak, A. Yu.、Khalilov, L. M.、Sultanmuratova, V. R.

  DOI：——

  日期：——
• TOLSTIKOV, G. A.;PROXOROVA, N. A.;SPIVAK, A. YU., 5 BCEC. KONF. PO METALLOORGAN. XIMII, YURMALA, 1-4 APR., 1991: TEZ. DOKL.+
  作者：TOLSTIKOV, G. A.、PROXOROVA, N. A.、SPIVAK, A. YU.

  DOI：——

  日期：——
• A Mitsunobu route to C-glycosides
  作者：Paolo Pasetto、Matthew C. Walczak

  DOI：10.1016/j.tet.2009.08.024

  日期：2009.10

  C-Glycosides were successfully prepared via dehydrative alkylation under Mitsunobu conditions, using substituted sulfonyl methanes as nucleophiles. The materials prepared were converted to useful C-glycoside intermediates. An application of this approach toward the synthesis of C-glycolipids is presented. (C) 2009 Elsevier Ltd. All rights reserved.